The Five Whys Start In Childhood: Why Surface Solutions Don't Solve Root Problems
Lesson 4 of 25 from podcast conversations with leaders who leave the world better than they found it
My sister Nancy told me this story that captures something we forget as adults:
She's teaching elementary school, and one of her students asks why the dishwasher is in the kitchen. Nancy could have said "because that's where it goes" and moved on.
Instead, she let the kid keep asking why.
Why is it in the kitchen? Because that's where we use dishes.
Why do we use dishes there? Because that's where we prepare and eat food.
Why do we prepare food in kitchens? Because of how modern houses are designed.
Because people started using big machines to do their jobs, which changed where and how we lived.
Five questions. From dishwasher to the industrial revolution.
Kids intuitively understand something we forget in organizational life: you have to go deep to understand anything.
The Problem With Surface-Level Strategy
I've sat through a lot of strategic planning sessions. They tend to follow a familiar pattern.
Someone identifies a problem: "We're struggling with staff retention."
The group brainstorms solutions: Better salaries. More benefits. Professional development opportunities. Recognition programs.
Someone gets tasked with implementing the solution. Everyone feels productive.
Six months later, retention is still a problem.
Here's why: we solved a symptom without understanding the root cause.
Maybe the retention problem isn't about compensation. Maybe it's about a culture where people feel micromanaged. Maybe it's about a leadership team that doesn't listen. Maybe it's about mission drift that leaves staff wondering if the work still matters.
You can't solve those problems with a raise.
But you won't discover those root causes unless you ask why. Multiple times. Until you get uncomfortable.
How The Five Whys Actually Work
The Five Whys is a technique developed by Toyota for root cause analysis. The concept is simple: when you encounter a problem, ask "why" five times to get past symptoms and reach the systemic issue.
Let me show you how this works with a common nonprofit challenge:
Problem: We can't find qualified candidates for our open roles.
Why? Because people don't know about our organization.
Why don't they know about us? Because we don't have the resources for marketing and outreach.
Why don't we have resources for that? Because our budget is stretched thin covering program costs.
Why is our budget stretched thin? Because we've been growing programs without growing infrastructure.
Why have we been growing without infrastructure? Because funders only want to pay for programs, not overhead.
Now you're at the root: this isn't a hiring problem. It's a funding model problem. You could post better job listings and still struggle, because the real issue is how you're resourced.
That's what asking "why" five times reveals: the problem you think you have often isn't the actual problem.
Why Organizations Stop At Two
In practice, most organizations don't make it past the second "why."
The first why gets you to an immediate cause. The second why starts to feel uncomfortable because it implicates decisions leadership has made. The third why reveals systemic issues that feel too big to tackle.
So we stop. We solve the surface problem. We feel productive. And six months later, we're frustrated that the same issue keeps coming back.
I've done this. I'd bet you have too.
Someone on your team raises a concern. You immediately jump to solutions. You fix the immediate irritant. You move on.
But that team member is still frustrated. Because the thing they raised wasn't actually the thing bothering them—it was just the most visible symptom of a deeper issue.
Going deep requires patience. It requires genuine curiosity rather than rushing to solutions. It requires being willing to discover uncomfortable truths about how your organization actually operates.
But that's where real problem-solving happens.
The Exercise That Changes Everything
Here's what I want you to do this week:
Identify your organization's biggest challenge right now. The thing that keeps coming up in meetings. The persistent problem that never seems to get fully resolved.
Write it down as a clear statement. "We struggle with [X]."
Now ask why. Five times.
Write down each answer before moving to the next question. Don't edit yourself. Don't jump to solutions. Just follow the chain of causation.
If you get stuck before five whys—if you hit a wall where you genuinely can't go deeper—that tells you something important: you don't understand the problem well enough yet.
Which means any solution you implement is probably treating a symptom rather than addressing root cause.
When you can get to five whys—when you can trace the chain from surface symptom to systemic root—that's when you're ready to solve the actual problem.
What Happens When You Go Deep
Nancy's student didn't need to understand the industrial revolution to use a dishwasher. But that deeper understanding changed how the kid thought about houses, design, and how we live.
The same thing happens when organizations ask why enough times.
You start a conversation about improving program delivery and end up realizing you need to rethink your entire funding model.
You start trying to fix a communication problem and discover it's actually about trust and decision-making authority.
You start addressing what looks like a capacity issue and find out it's really about strategic clarity—people are working hard, just not on the right things.
Going deep is uncomfortable because it reveals that the easy fix won't work. That the solution requires more fundamental change than you wanted to admit.
But that discomfort is exactly where transformation becomes possible.
From Symptoms To Systems
Kids ask why because they're genuinely trying to understand how the world works. They're not looking for quick answers—they're building mental models.
We need that same curiosity in organizational strategy.
Not "what's the fastest solution" but "what's actually causing this?"
Not "how do we make this go away" but "what system is creating this symptom?"
Not "who can we blame" but "what patterns keep producing this outcome?"
Surface solutions feel productive. They're easy to implement, easy to check off the list, easy to report to the board.
But they don't create change.
Real change requires going deep enough to understand what's actually happening. And that starts with asking why. At least five times.
Until you get uncomfortable.
That's where the real answers live.
This is lesson 4 in a 25-part series exploring insights from podcast conversations with leaders who leave the world better than they found it.
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